Caretaker: The redfin of brokers. Take all the value for themselves freeze out the brokers (who provide a service but are universally disdained). Ride that wave of positive news for a couples years. Eventually everyone will hate the fraction of the market Caretaker has as they raise prices to make investors happy and people realize there are problems. It's like the same idea of Uber and Lyft. Less human involvement =…
...why sarcasm?
The entire premise of technological and economic progress is outsourcing repetitive mind-numbing tasks (whether farming or showing apartments) to automation.
You're just describing regular old beneficial economic progress -- the reason why we're not all still farmers.
And if Caretaker becomes a massive success, then competitors will appear, which is the basic economic force that prevents prices from rising too far. All of which would be wonderful.